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Chesapeake Bay Cruising

Cruising the Chesapeake: Your Weekly Guide to Bay Destinations

August 10, 2025

The Chesapeake Bay isn’t just the largest estuary in the United States — it’s a boater’s paradise.
From bustling port cities to quiet anchorages tucked away on the Eastern Shore, the Bay offers an incredible variety of destinations, each with its own charm, history, and character.

Over the next several weeks, I’ll be sharing a series of in-depth destination reviews based on my own experiences cruising these waters. Whether you’re planning a weekend getaway, an extended voyage, or you’re just looking for your next great marina stop, these guides will help you plan your trip with confidence.

What to Expect in Each Review

Each weekly article will cover:

  • Approach & Navigation – Tips for entering harbors and avoiding hazards
  • Docking & Anchorages – Where to tie up, drop the hook, and find services
  • Fuel, Water & Provisions – The best spots to refuel and restock
  • Things to Do Ashore – Local restaurants, attractions, and hidden gems
  • Boater Tips – When to visit, seasonal considerations, and local quirks
  • Quick Reference Table – VHF channels, depths, transient rates, and amenities at a glance

The Chesapeake Stops We’ll Explore

Here’s the itinerary for this series:

  1. Deltaville, VA – The Boating Capital of the Chesapeake
  2. Cape Charles, VA – Small-Town Charm with a Big Marina Scene
  3. Norfolk, VA – Big City Amenities with Naval History
  4. Yorktown, VA – History, Hospitality, and Riverfront Beauty
  5. Onancock, VA – A Quiet Eastern Shore Escape
  6. Crisfield, MD – The Crab Capital Welcomes Boaters
  7. Solomons, MD – Gateway to the Patuxent
  8. Kilmarnock, VA – Cozy Northern Neck Cruising
  9. Irvington, VA – Boutique Shops and Coastal Relaxation

Why Follow Along?

The Bay is ever-changing — weather, facilities, and even favorite restaurants can shift from season to season. My goal is to give you up-to-date, practical information mixed with the personal touches only a fellow boater can provide.

Whether you’re a seasoned cruiser or a weekend gunkholer, this series will help you:

  • Discover new destinations
  • Avoid common docking and anchoring challenges
  • Find the best local eats and activities
  • Make the most of your time on the water

Coming Up Next Week

We’ll kick things off with Deltaville, VA — a community known as The Boating Capital of the Chesapeake for good reason.
From world-class boatyards to quiet anchorages and friendly locals, it’s a stop no cruiser should miss.